Actually I came accross PG's essays before I discovered YC. Historically I think he's right. Even the poorest ones in today's western world are still better of in most aspects than most of the richest ones back in, say, the 16th and 17th and even 18th century. Easily.
He even once wrote, no idea in which essays, that he would prefer to be poor in an advanced society to be rich in an non-advanced one (something along these lines). Now, as we know that automation and software are enabling companies, and their investors / founders (with VCs investors more than founders IMHO), to create a lot of whealth that is not very well distributed across society. Which we see every day. So, working from his earlier statement on which society he would rather life in had he the choice, I assume PG has some level of understanding about the social realities. He is now also in a position to actually do something about it, him being arguably very rich and influential in his own way.
And what is he doing? Arguing against taxes for the rich to make life easier for the poor, against reducing the economic and social distribution and faisness in society. Because, according to him as far as I understood his later essays, as long as everybody can be enabled to found a company that problem will go away. Which it will not, not everyone can start one, regardless of access to capital. And even then most of the return will end up in the hands of the rich investor class with founders being more often than not cogs in the system.
Call the opposite approch socialism if you want, but if we as a socuiety don't think about these issues, hard, we will end up in deep trouble. Not just in the US where these problems are way more extreme than in Europe. I'm just way beyond believing that rich people will voluntarily do something about the poor if it would cost them a single dime.